Acetyl chloride → HCID 12940596, compound

HRID 1577167Notes

Reaction equation

HRID 1577167 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:19](Cl)(=[O:21])[CH3:20]>C(=S)=S>[C:19]([C:9]1[CH:8]=[CH:7][C:6]([O:5][C:4]2[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:3]=2[C:2]([F:1])([F:17])[F:18])=[CH:11][CH:10]=1)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 20570460HCID 20570460, compound

Product 1

HCID 12940596HCID 12940596, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

In this preparation 23.18 g (0.085 mol) of 4-(2-trifluoromethyl-4-chlorophenoxy)-benzene and 6.66 g (0.085 mol) of acetyl chloride are admixed with 200 ml of carbon disulfide and then 27.52 g (0.17 mol) of ferric chloride is added and the resulting mixture stirred at room temperature for about 23 hours. The mixture is then washed three times with ice-water, dried over magnesium sulfite and filtered. The filtrate is evaporated to dryness and the residue chromatographed on a silica gel column eluting with hexane; 5 vol.% tetrahydrofuran-hexane; and then 10 vol.% tetrahydrofuran-hexane, affording 1-acetyl-4-(2-trifluoromethyl-4-chlorophenoxy)-benzene.

Workup

  1. washThe mixture is then washed three times with ice-water
  2. dry with materialdried over magnesium sulfite
  3. filtrationfiltered
  4. customThe filtrate is evaporated to dryness
  5. customthe residue chromatographed on a silica gel column
  6. washeluting with hexane

Sources & evidence

ORD record
ord-22fd31c9cbdb45f78ea02582491e3170
Source dataset
uspto-grants-1981_09
Patent number
US04287213

Reaction notes

Loading…